Tetrahydrofuran → 1-(3-Fluorophenyl)propan-1-ol
Reaktionsgleichung
[F:1][C:2]1[CH:3]=C(C(C)C(O)=O)C=C[CH:7]=1.B.[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1.[CH2:19]1COC[CH2:20]1>>[F:1][C:2]1[CH:7]=[C:14]([CH:18]([OH:17])[CH2:19][CH3:20])[CH:15]=[CH:16][CH:3]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
3-Fluorophenylpropionic acid (39, 0.500 g, 2.97 mmol) was diluted in anhydrous THF (2 mL) under argon, and cooled to 0° C. Borane-THF (1 M, 4.16 mL, 4.16 mmol) was added dropwise, and the mixture was allowed to warm to room temperature and stirred for 18 h. The reaction was quenched by the addition of 1:1 THF/H2O (5 mL). When gas evolution ceased, solid K2CO3 was added until the mixture separated into two layers, which were separated. The aqueous layer was extracted with EtOAc (2×5 mL), and the combined organic layers were washed with H2O (15 mL) and sat. aq. NaCl (15 mL), dried over anhydrous sodium sulfate, and concentrated to yield the product as a clear oil (0.446 g, 97%) after drying in vacuo. 1H-NMR (500 MHz; CDCl3): δ 7.29-7.25 (m, 1 H), 7.00 (d, J=7.6 Hz, 1 H), 6.95-6.89 (m, 2 H), 3.71 (t, J=6.4 Hz, 2 H), 2.74 (t, J=7.7 Hz, 2 H), 1.95-1.89 (m, 2 H), 1.39 (s, 1 H).